How does a techie/filmmaker/magician pop the big question?

How do you surprise someone who wants to be surprised? That’s the problem I faced proposing to my girlfriend. If I did anything out of the ordinary, she’d be suspicious.

I knew I wanted to do it around New Year’s — which would give us enough time to have a summer wedding — but as that day grew closer, I still found myself without any good ideas. Should I use some of my old childhood magic skills to make the ring “appear” somewhere unexpected? Should I use some tricks I learned in film school to do it with a heartfelt video? At the time, I was just getting into the tech consulting biz. Should I do something high tech?

Three days before my target date (Saturday, Jan. 1st), we went out for sushi. My eyes kept wandering onto a TV in a corner of the restaurant. And it hit me. I pictured us sitting down to watch a Netflix movie at home. Mid-way through the flick, a character would get down on one knee to propose to another, and that’s when I’d get up, walk to the TV, reach into the film, and pull the ring out of the movie world and into ours. And then I’d propose with THE RING THAT WAS JUST IN THE MOVIE. No way she’d see that coming.

I had no idea how I’d do it exactly, but I knew it’d require a little bit of magic, a little bit of filmmaking, and a little bit of techie know-how. As soon as I got home, I started working on the following plan:

On Saturday, when I’m at her place, we’d get a disc in the mail from Netflix. But what disc? It’d have to be both a movie that’d realistically be on our Netflix cue, but also something with a half-decent proposal scene. I rented a bunch of DVDs, scanned through a bunch of movies, and settled on…

Leap Year, starring Amy Adams. It was a romantic comedy that came out within the last year that neither of us saw in theaters, so it could realistically be on our Netflix cue. It had a proposal-like scene in the 1st ten minutes. Perfect. I’m not going to wait two hours to do this thing. Also, Melissa always falls asleep twenty minutes into every movie we sit down to watch together. I mean always. I had to beat the clock.

I’d rip open the envelope, pop the disc into the DVD player, and we’d sit back to watch the movie. Ten minutes later, Amy Adams and Adam Scott would be on the TV, dining at a super-fancy restaurant, where Amy thinks Adam is going to propose to her (Spoiler Alert: He’s not, but Melissa doesn’t know that). So basically, their situation is the exact opposite of ours in every way.

Adam reaches into his pocket, pulls out a small jewelry box, and places it on the table.

Amy looks down at the box and lights up. This is the moment her character has been waiting for her entire life.

And it’s at that exact moment the DVD will start to get glitchy…

After a moment of skipping, the DVD will freeze on the image of a jewelry box on a restaurant table.

Melissa will think the DVD is scratched. I’d say “let me take a look at it.”

Then, as I reached behind the TV to “fix” it, Melissa will see…

…my hand and arm, reaching into the movie, grabbing the jewelry box, and pulling it out into the real world.

At least that was the plan. And for the most part, that’s how it went down. Read on to find out how I did it, what went right, and what went wrong…

I woke up Thursday with that plan in mind, ready to go. I didn’t have a back-up plan, so I knew I had to make it work. I spent all morning watching a ton of movies to find one that’d fit my criteria. This wound up being the single hardest part of the process. Not only did the proposal have to happen early, but I knew I didn’t have time to do any fancy visual effects work. The movie needed a clear, steady shot of a ring, or at least a ring box. Movement, hands, faces — the more stuff in the shot the more complicated it’d be to recreate. The simpler the better.

As soon as I knew Leap Year was the winner, I added it to my Netflix cue and made sure it’d be the next disc to arrive on Saturday. Why didn’t I want to propose on Friday, New Year’s Eve, at the stroke of midnight? Because she’d be expecting that. So to throw her off, I let her make all the plans for that weekend. She made restaurant reservations, she could pick any parties we’d go to. She’d do it all. The more she planned, the less she’d be expecting me to do anything special.

Though I planned to do it Saturday, I still only had one day to prepare this proposal because we’d be spending most of Friday together. I had to finish this all on Thursday.

So Thursday afternoon, I set about recreating that Leap Year scene in my apartment. I didn’t have to recreate the entire restaurant, or even a part of it. I just had to create a shot of a table that could be the table from the restaurant. If you watch the actual movie, the one fleeting moment where you see the jewelry box on the table doesn’t even come close to my set-up. But it doesn’t matter. Melissa would never see that shot (until later).

I then set up a camcorder and simply filmed my hand reaching into the shot and grabbing the ring box. Nothing fancy. This was the easiest part of the whole project. The next two steps would be a smidgeon more difficult…

Get that shot onto the DVD.

Get that DVD mailed to me from the Netflix corporation.

So late Thursday afternoon I set out about ripping the first ten minutes of the movie onto my computer (the only portion of the movie I needed). First, I used Google to find a good program to do that, and second, I prayed that this constituted “fair use” as far as copyright law is concerned. I love Melissa, but I’m not going to jail for her.

I then imported the real Leap Year footage and my home-made video into Final Cut Pro. At the moment in the film I wanted to become glitchy, I played around with some filters and made some odd edits to create the appearance the DVD was scratched. You know, some digital artifacting followed by some skipping, followed by some freezing on a single frame. All that would hide the jarring cut from the movie’s $100,000 restaurant set to my $10 one.

I then inserted the shot of my hand reaching into frame and grabbing the box, and — for ambiance — I added some music to accompany the live proposal (Pachebel’s Canon). I also left myself some time between when the video starts glitching up and when my hand appears so I’d have time to get into position.

Next step is burning all that onto a DVD… but something’s still missing. I can’t just pop an allegedly commercial DVD into a DVD player and go straight to the movie. I needed some menus. I’m sure there’s a way to co-opt the menus from the actual DVD, but I figured it’d be easier to just make my own using iDVD. And that’s what I did. I found promotional images of the movie on the web, scattered them all about one of that program’s pre-made menus, and even added some links to some non-existent “special features.” Considering it took just ten minutes, I think it looked pretty good. Then I finally burned the DVD. Done. The rest would take place at Melissa’s apartment.

As soon as I got to her place (and was alone), I taped the ring box (with the engagement ring in it) to the back of her TV. I mean, something had to be there when I reached behind the set. Then I’d place the rigged-DVD under her DVD player. That way, after we got the Netflix envelope in the mail on Saturday, I could open it right in front of her. She’d see the actual DVD. She’d see me walk to the DVD player to pop it in. And (with my back to her) that’s when I’d swap the fake one for the real one. That’s a hell of a lot easier then getting the fake one into that envelope in the first place. It’s all magic and misdirection, really.

And that was my plan. What could go wrong?

On Friday the 31st, as I packed up to head over to her place for the weekend, I realized something I really should’ve realized much, much sooner… There’s no mail delivery on January 1st. And there’d be no mail on the next day, a Sunday, either. Leap Year wouldn’t be arriving in a Netflix envelope until Monday at the earliest.

Oops.

That’s much too late.

So I quickly improvised a plan B. I had sitting around my apartment all these movies I’d rented for research (the ones I was scanning for proposal scenes). I picked them all up and took them with me.

“What are all these movies for?” She asked when I arrived.

“Well, I know we wanted to watch some Netflix movies this weekend, but I realized that Netflix won’t be delivering anything ’til Monday, so I went to Blockbuster and rented some movies over for us to watch.”

Did I really want to watch all these movies? No. But I knew bringing over a bunch of movies would be less suspicious than bringing just one over. She said “good thinking” and that was that.

So we went to dinner on Friday night. She picked the place. Capital Grille. Our plan was to stay there until Midnight, celebrate with everyone else in the restaurant, then head home. No parties. No proposal. It’d be a low-key New Year’s Eve.

Except dinner ended an hour too early.

It’s 11pm, we’ve finished dinner and dessert. Neither of us felt like just sitting there for another hour. So we went home. And that’s when I knew I had my opportunity, an opportunity I didn’t think I’d ever have. It’s New Year’s Eve and I knew if I could make her say “hey, let’s watch a movie” before midnight, it’d be the first NYE proposal in the history of NYE proposals that’d actually be a surprise. (Tip for every guy out there in a serious relationship: Every holiday, she’s thinking “this is it.” Especially NYE.)

We got changed from our dressy clothes. She got into her PJs. I got into something more casual — i.e. the shirt I’d have to wear to match the arm in the video.

We sat on the couch and put on one of the NYE countdown shows. It was just as insufferable as I was hoping it’d be.

“You want to watch this, or maybe something else?” I suggested.

She wisely opted for any of the movies I brought over. Then, like any good magician trying to force a particular card onto an unsuspecting soul — you really think when they say “pick a card, any card,” you actually have a choice? — I encouraged her to pick Leap Year without making it look like I was encouraging her to pick Leap Year.

And she picked Leap Year. Thank God. If she had picked Bride Wars this proposal was going to turn into a double homicide.

In went the movie at about 11:45pm.

Now, I really wish I could’ve videotaped what came next. But there’s no way I could’ve hidden a camcorder in her place to film the entire thing without blowing the whole operation. So you’ll just have to trust me that it worked beyond belief. By midnight on New Year’s Eve, I was down on my knee, proposing with a ring that just one minute earlier was IN A FRIGGIN’ MOVIE.

And she said “yes.”

And then came the second most memorable part of the night…

I got food poisoning. About twenty minutes after the proposal, I was throwing up in the bathroom. For the rest of the weekend, I was incapacitated, in bed, unable to move. Fortuitously, the proposal wound up happening during the only window of time it could’ve happened that weekend. Seven months later, we were married. We just got back from our honeymoon.